#------------------------------------------------------------------------------
#$Date: 2017-06-04 17:50:26 +0300 (Sun, 04 Jun 2017) $
#$Revision: 197345 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/25/4032554.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4032554
loop_
_publ_author_name
'Jarvis, Tia S.'
'Collins, Carleton G.'
'Dempsey, Janel M.'
'Oliver, Allen G.'
'Smith, Bradley D.'
_publ_section_title
;
 Synthesis and Structure of 3,3-Dimethylindoline Squaraine Rotaxanes.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5819
_journal_page_last               5825
_journal_paper_doi               10.1021/acs.joc.7b00655
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C56 H52 N4 O4, C28 H28 N2 O4'
_chemical_formula_sum            'C84 H80 N6 O8'
_chemical_formula_weight         1301.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 112.420(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9997(5)
_cell_length_b                   25.0507(12)
_cell_length_c                   13.0048(6)
_cell_measurement_reflns_used    5782
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.94
_cell_measurement_theta_min      3.53
_cell_volume                     3312.6(3)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.229
_diffrn_reflns_theta_min         3.529
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       plate
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6502
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1360P)²+2.8970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2227
_refine_ls_wR_factor_ref         0.2358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5314
_reflns_number_total             6502
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b00655_si_002.cif
_cod_data_source_block           nd1604
_cod_database_code               4032554
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.874
_shelx_estimated_absorpt_t_max   0.985
_diffrn_source_monochromator     'MONTEL Multi-layer'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.52435(19) 0.41238(7) 0.46845(14) 0.0380(4) Uani 1 1 d . . . . .
O2 O 0.1271(3) 0.75313(10) -0.03171(19) 0.0675(7) Uani 1 1 d . . . . .
N1 N 0.3811(2) 0.61006(9) 0.30206(18) 0.0374(5) Uani 1 1 d . . . . .
H1 H 0.4083 0.6131 0.3748 0.045 Uiso 1 1 calc R U . . .
C1 C 0.5119(2) 0.46067(10) 0.4860(2) 0.0314(5) Uani 1 1 d . . . . .
C2 C 0.4736(2) 0.50798(10) 0.4151(2) 0.0313(5) Uani 1 1 d . . . . .
C3 C 0.4380(2) 0.51687(10) 0.3019(2) 0.0339(5) Uani 1 1 d . . . . .
H3 H 0.4452 0.4879 0.2573 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3925(2) 0.56549(10) 0.2496(2) 0.0342(5) Uani 1 1 d . . . . .
C5 C 0.3464(3) 0.57709(11) 0.1243(2) 0.0362(5) Uani 1 1 d . . . . .
C6 C 0.2923(3) 0.63307(11) 0.1194(2) 0.0381(6) Uani 1 1 d . . . . .
C7 C 0.3207(3) 0.65138(11) 0.2270(2) 0.0387(6) Uani 1 1 d . . . . .
C8 C 0.2862(3) 0.70208(12) 0.2487(2) 0.0469(7) Uani 1 1 d . . . . .
H8 H 0.3064 0.7141 0.3227 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2209(3) 0.73463(12) 0.1577(3) 0.0507(7) Uani 1 1 d . . . . .
H9 H 0.1955 0.7696 0.1696 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1923(3) 0.71699(13) 0.0504(3) 0.0523(7) Uani 1 1 d . . . . .
C11 C 0.2272(3) 0.66564(12) 0.0295(2) 0.0435(6) Uani 1 1 d . . . . .
H11 H 0.2068 0.6535 -0.0444 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2472(3) 0.53626(12) 0.0503(2) 0.0429(6) Uani 1 1 d . . . . .
H12A H 0.2914 0.5019 0.0540 0.064 Uiso 1 1 calc R U . . .
H12B H 0.2118 0.5490 -0.0267 0.064 Uiso 1 1 calc R U . . .
H12C H 0.1753 0.5318 0.0764 0.064 Uiso 1 1 calc R U . . .
C13 C 0.4660(3) 0.57798(12) 0.0898(2) 0.0433(6) Uani 1 1 d . . . . .
H13A H 0.5297 0.6045 0.1346 0.065 Uiso 1 1 calc R U . . .
H13B H 0.4368 0.5874 0.0109 0.065 Uiso 1 1 calc R U . . .
H13C H 0.5072 0.5426 0.1020 0.065 Uiso 1 1 calc R U . . .
C14 C 0.0607(4) 0.73339(14) -0.1387(3) 0.0616(9) Uani 1 1 d . . . . .
H14A H 0.1238 0.7167 -0.1654 0.092 Uiso 1 1 calc R U . . .
H14B H 0.0158 0.7628 -0.1884 0.092 Uiso 1 1 calc R U . . .
H14C H -0.0041 0.7068 -0.1375 0.092 Uiso 1 1 calc R U . . .
O3 O 0.0731(2) 0.38183(13) 0.0922(2) 0.0726(8) Uani 1 1 d . . . . .
O4 O 0.7536(2) 0.35772(10) 0.20792(18) 0.0515(5) Uani 1 1 d . . . . .
N2 N 0.2043(2) 0.40136(10) 0.2660(2) 0.0480(6) Uani 1 1 d . . . . .
H2N H 0.2853 0.4053 0.3148 0.058 Uiso 1 1 calc R U . . .
N3 N 0.7027(2) 0.38181(10) 0.3534(2) 0.0439(6) Uani 1 1 d . . . . .
H3N H 0.6411 0.3859 0.3805 0.053 Uiso 1 1 calc R U . . .
C15 C 0.0936(3) 0.41646(14) 0.2960(4) 0.0650(11) Uani 1 1 d . . . . .
H15A H 0.0722 0.3861 0.3349 0.078 Uiso 1 1 calc R U . . .
H15B H 0.0159 0.4233 0.2271 0.078 Uiso 1 1 calc R U . . .
C16 C 0.1836(3) 0.38172(12) 0.1657(3) 0.0448(6) Uani 1 1 d . . . . .
C17 C 0.2986(3) 0.35962(11) 0.1451(2) 0.0396(6) Uani 1 1 d . . . . .
C18 C 0.4280(2) 0.37234(10) 0.2102(2) 0.0335(5) Uani 1 1 d . . . . .
H18 H 0.4471 0.3960 0.2716 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5293(3) 0.35043(10) 0.1854(2) 0.0357(5) Uani 1 1 d . . . . .
C20 C 0.5012(3) 0.31489(12) 0.0972(2) 0.0462(7) Uani 1 1 d . . . . .
H20 H 0.5712 0.3005 0.0801 0.055 Uiso 1 1 calc R U . . .
C21 C 0.3721(3) 0.29995(12) 0.0333(3) 0.0522(7) Uani 1 1 d . . . . .
C22 C 0.2720(3) 0.32382(12) 0.0575(2) 0.0498(7) Uani 1 1 d . . . . .
H22 H 0.1831 0.3155 0.0130 0.060 Uiso 1 1 calc R U . . .
C23 C 0.6704(3) 0.36387(11) 0.2496(2) 0.0389(6) Uani 1 1 d . . . . .
C24 C 0.8401(3) 0.39472(15) 0.4230(3) 0.0539(8) Uani 1 1 d . . . . .
H24A H 0.8891 0.4018 0.3745 0.065 Uiso 1 1 calc R U . . .
H24B H 0.8813 0.3636 0.4705 0.065 Uiso 1 1 calc R U . . .
C25 C 0.8503(2) 0.44280(13) 0.4958(2) 0.0433(6) Uani 1 1 d . . . . .
C26 C 0.8234(2) 0.49352(14) 0.4468(3) 0.0486(7) Uani 1 1 d . . . . .
C27 C 0.7895(3) 0.50081(19) 0.3299(3) 0.0662(10) Uani 1 1 d . . . . .
H27 H 0.7834 0.4706 0.2841 0.079 Uiso 1 1 calc R U . . .
C28 C 0.7663(4) 0.5495(3) 0.2839(4) 0.0865(16) Uani 1 1 d . . . . .
H28 H 0.7483 0.5532 0.2068 0.104 Uiso 1 1 calc R U . . .
C29 C 0.7679(4) 0.5944(2) 0.3456(5) 0.0958(19) Uani 1 1 d . . . . .
H29 H 0.7471 0.6282 0.3103 0.115 Uiso 1 1 calc R U . . .
C30 C 0.8001(3) 0.59009(17) 0.4598(5) 0.0787(13) Uani 1 1 d . . . . .
H30 H 0.7997 0.6211 0.5018 0.094 Uiso 1 1 calc R U . . .
C31 C 0.8335(3) 0.54014(13) 0.5140(3) 0.0515(8) Uani 1 1 d . . . . .
C32 C 0.8803(3) 0.53464(12) 0.6304(3) 0.0482(7) Uani 1 1 d . . . . .
C33 C 0.9104(2) 0.48420(12) 0.6795(2) 0.0424(6) Uani 1 1 d . . . . .
C34 C 0.9639(3) 0.47724(16) 0.7973(3) 0.0558(8) Uani 1 1 d . . . . .
H34 H 0.9777 0.5078 0.8438 0.067 Uiso 1 1 calc R U . . .
C35 C 0.9954(3) 0.42852(19) 0.8448(3) 0.0654(10) Uani 1 1 d . . . . .
H35 H 1.0344 0.4255 0.9235 0.078 Uiso 1 1 calc R U . . .
C36 C 0.9710(3) 0.38306(16) 0.7796(3) 0.0606(9) Uani 1 1 d . . . . .
H36 H 0.9901 0.3490 0.8142 0.073 Uiso 1 1 calc R U . . .
C37 C 0.9199(3) 0.38633(13) 0.6658(3) 0.0531(8) Uani 1 1 d . . . . .
H37 H 0.9033 0.3545 0.6228 0.064 Uiso 1 1 calc R U . . .
C38 C 0.8909(2) 0.43713(11) 0.6104(2) 0.0405(6) Uani 1 1 d . . . . .
C39 C 0.3433(4) 0.25827(14) -0.0599(3) 0.0675(10) Uani 1 1 d . . . . .
C40A C 0.1911(7) 0.2336(3) -0.0847(6) 0.0498(15) Uiso 0.459(3) 1 d . . P A 1
H40A H 0.1907 0.2161 -0.0175 0.075 Uiso 0.459(3) 1 calc R U P A 1
H40B H 0.1271 0.2629 -0.1054 0.075 Uiso 0.459(3) 1 calc R U P A 1
H40C H 0.1675 0.2077 -0.1457 0.075 Uiso 0.459(3) 1 calc R U P A 1
C41A C 0.4325(10) 0.2138(4) -0.0310(9) 0.065(3) Uiso 0.459(3) 1 d . . P A 1
H41A H 0.4343 0.1976 0.0382 0.097 Uiso 0.459(3) 1 calc R U P A 1
H41B H 0.4032 0.1872 -0.0908 0.097 Uiso 0.459(3) 1 calc R U P A 1
H41C H 0.5209 0.2262 -0.0206 0.097 Uiso 0.459(3) 1 calc R U P A 1
C42A C 0.3373(13) 0.2830(4) -0.1597(8) 0.068(2) Uiso 0.459(3) 1 d . . P A 1
H42A H 0.2758 0.3131 -0.1770 0.102 Uiso 0.459(3) 1 calc R U P A 1
H42B H 0.4249 0.2960 -0.1505 0.102 Uiso 0.459(3) 1 calc R U P A 1
H42C H 0.3072 0.2571 -0.2207 0.102 Uiso 0.459(3) 1 calc R U P A 1
C40B C 0.2120(13) 0.2484(5) -0.1291(11) 0.066(3) Uiso 0.316(3) 1 d . . P A 2
H40D H 0.1682 0.2823 -0.1593 0.099 Uiso 0.316(3) 1 calc R U P A 2
H40E H 0.2090 0.2250 -0.1903 0.099 Uiso 0.316(3) 1 calc R U P A 2
H40F H 0.1668 0.2312 -0.0860 0.099 Uiso 0.316(3) 1 calc R U P A 2
C41B C 0.4164(12) 0.2065(4) -0.0103(9) 0.035(2) Uiso 0.316(3) 1 d . . P A 2
H41D H 0.5076 0.2149 0.0374 0.052 Uiso 0.316(3) 1 calc R U P A 2
H41E H 0.3731 0.1889 0.0338 0.052 Uiso 0.316(3) 1 calc R U P A 2
H41F H 0.4153 0.1828 -0.0705 0.052 Uiso 0.316(3) 1 calc R U P A 2
C42B C 0.4176(13) 0.2756(5) -0.1477(10) 0.059(3) Uiso 0.316(3) 1 d . . P A 2
H42D H 0.5107 0.2832 -0.1047 0.088 Uiso 0.316(3) 1 calc R U P A 2
H42E H 0.4099 0.2462 -0.1995 0.088 Uiso 0.316(3) 1 calc R U P A 2
H42F H 0.3750 0.3076 -0.1896 0.088 Uiso 0.316(3) 1 calc R U P A 2
C40C C 0.4881(19) 0.2466(8) -0.0836(17) 0.074(5) Uiso 0.225(3) 1 d . . P A 3
H40G H 0.5045 0.2769 -0.1243 0.110 Uiso 0.225(3) 1 calc R U P A 3
H40H H 0.5622 0.2426 -0.0122 0.110 Uiso 0.225(3) 1 calc R U P A 3
H40I H 0.4781 0.2140 -0.1275 0.110 Uiso 0.225(3) 1 calc R U P A 3
C41C C 0.360(3) 0.2087(10) -0.004(2) 0.092(7) Uiso 0.225(3) 1 d . . P A 3
H41G H 0.4141 0.2136 0.0746 0.138 Uiso 0.225(3) 1 calc R U P A 3
H41H H 0.2736 0.1946 -0.0124 0.138 Uiso 0.225(3) 1 calc R U P A 3
H41I H 0.4032 0.1835 -0.0372 0.138 Uiso 0.225(3) 1 calc R U P A 3
C42C C 0.284(2) 0.2868(7) -0.1673(14) 0.057(4) Uiso 0.225(3) 1 d . . P A 3
H42G H 0.3066 0.3248 -0.1562 0.086 Uiso 0.225(3) 1 calc R U P A 3
H42H H 0.3175 0.2717 -0.2208 0.086 Uiso 0.225(3) 1 calc R U P A 3
H42I H 0.1880 0.2828 -0.1960 0.086 Uiso 0.225(3) 1 calc R U P A 3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C10 O2 C14 117.5(3) . .
C4 N1 C7 111.9(2) . .
C4 N1 H1 124.1 . .
C7 N1 H1 124.1 . .
O1 C1 C2 134.1(2) . .
O1 C1 C2 134.3(2) . 3_666
C2 C1 C2 91.6(2) . 3_666
O1 C1 C1 179.0(2) . 3_666
C2 C1 C1 45.82(14) . 3_666
C2 C1 C1 45.78(14) 3_666 3_666
C3 C2 C1 134.1(2) . .
C3 C2 C1 137.5(2) . 3_666
C1 C2 C1 88.4(2) . 3_666
C2 C3 C4 124.2(2) . .
C2 C3 H3 117.9 . .
C4 C3 H3 117.9 . .
N1 C4 C3 124.6(2) . .
N1 C4 C5 109.0(2) . .
C3 C4 C5 126.5(2) . .
C6 C5 C12 114.6(2) . .
C6 C5 C4 100.6(2) . .
C12 C5 C4 114.0(2) . .
C6 C5 C13 109.8(2) . .
C12 C5 C13 107.9(2) . .
C4 C5 C13 109.7(2) . .
C11 C6 C7 120.1(3) . .
C11 C6 C5 130.6(2) . .
C7 C6 C5 109.3(2) . .
C8 C7 C6 122.3(2) . .
C8 C7 N1 129.0(2) . .
C6 C7 N1 108.7(2) . .
C7 C8 C9 117.2(3) . .
C7 C8 H8 121.4 . .
C9 C8 H8 121.4 . .
C10 C9 C8 121.2(3) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
O2 C10 C9 115.1(3) . .
O2 C10 C11 123.8(3) . .
C9 C10 C11 121.1(3) . .
C6 C11 C10 118.1(3) . .
C6 C11 H11 120.9 . .
C10 C11 H11 120.9 . .
C5 C12 H12A 109.5 . .
C5 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C5 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C5 C13 H13A 109.5 . .
C5 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C5 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 C14 H14A 109.5 . .
O2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 N2 C15 120.6(3) . .
C16 N2 H2N 119.7 . .
C15 N2 H2N 119.7 . .
C23 N3 C24 120.7(2) . .
C23 N3 H3N 119.7 . .
C24 N3 H3N 119.7 . .
N2 C15 C32 113.7(2) . 3_666
N2 C15 H15A 108.8 . .
C32 C15 H15A 108.8 3_666 .
N2 C15 H15B 108.8 . .
C32 C15 H15B 108.8 3_666 .
H15A C15 H15B 107.7 . .
O3 C16 N2 120.8(3) . .
O3 C16 C17 121.1(3) . .
N2 C16 C17 118.2(2) . .
C18 C17 C22 119.6(3) . .
C18 C17 C16 123.1(2) . .
C22 C17 C16 117.2(3) . .
C19 C18 C17 119.7(2) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
C18 C19 C20 120.0(3) . .
C18 C19 C23 122.5(2) . .
C20 C19 C23 117.5(2) . .
C19 C20 C21 121.3(3) . .
C19 C20 H20 119.4 . .
C21 C20 H20 119.4 . .
C22 C21 C20 117.6(3) . .
C22 C21 C39 121.8(3) . .
C20 C21 C39 120.6(3) . .
C21 C22 C17 121.7(3) . .
C21 C22 H22 119.1 . .
C17 C22 H22 119.1 . .
O4 C23 N3 121.9(3) . .
O4 C23 C19 120.8(2) . .
N3 C23 C19 117.3(2) . .
N3 C24 C25 112.0(2) . .
N3 C24 H24A 109.2 . .
C25 C24 H24A 109.2 . .
N3 C24 H24B 109.2 . .
C25 C24 H24B 109.2 . .
H24A C24 H24B 107.9 . .
C38 C25 C26 120.4(3) . .
C38 C25 C24 120.5(3) . .
C26 C25 C24 119.0(3) . .
C25 C26 C27 121.5(3) . .
C25 C26 C31 120.4(3) . .
C27 C26 C31 118.1(3) . .
C28 C27 C26 121.2(5) . .
C28 C27 H27 119.4 . .
C26 C27 H27 119.4 . .
C27 C28 C29 121.7(5) . .
C27 C28 H28 119.1 . .
C29 C28 H28 119.1 . .
C28 C29 C30 120.0(4) . .
C28 C29 H29 120.0 . .
C30 C29 H29 120.0 . .
C29 C30 C31 120.8(5) . .
C29 C30 H30 119.6 . .
C31 C30 H30 119.6 . .
C32 C31 C30 122.8(4) . .
C32 C31 C26 119.1(3) . .
C30 C31 C26 118.1(4) . .
C33 C32 C31 120.4(3) . .
C33 C32 C15 119.2(3) . 3_666
C31 C32 C15 120.3(3) . 3_666
C32 C33 C34 122.0(3) . .
C32 C33 C38 120.0(3) . .
C34 C33 C38 118.0(3) . .
C35 C34 C33 122.0(3) . .
C35 C34 H34 119.0 . .
C33 C34 H34 119.0 . .
C34 C35 C36 120.4(3) . .
C34 C35 H35 119.8 . .
C36 C35 H35 119.8 . .
C37 C36 C35 121.1(3) . .
C37 C36 H36 119.4 . .
C35 C36 H36 119.4 . .
C36 C37 C38 121.0(3) . .
C36 C37 H37 119.5 . .
C38 C37 H37 119.5 . .
C25 C38 C37 123.1(3) . .
C25 C38 C33 119.5(3) . .
C37 C38 C33 117.3(3) . .
C42A C39 C41A 111.6(7) . .
C41C C39 C42C 146.1(13) . .
C40B C39 C41B 111.6(7) . .
C40B C39 C21 118.5(6) . .
C41C C39 C21 104.3(11) . .
C42A C39 C21 110.4(5) . .
C41A C39 C21 113.9(5) . .
C42C C39 C21 107.4(7) . .
C41B C39 C21 109.0(5) . .
C40B C39 C42B 104.9(7) . .
C41B C39 C42B 100.9(7) . .
C21 C39 C42B 110.4(5) . .
C42A C39 C40A 106.7(6) . .
C41A C39 C40A 107.1(6) . .
C21 C39 C40A 106.8(4) . .
C41C C39 C40C 89.7(14) . .
C42C C39 C40C 91.1(10) . .
C21 C39 C40C 108.8(7) . .
C39 C40A H40A 109.5 . .
C39 C40A H40B 109.5 . .
H40A C40A H40B 109.5 . .
C39 C40A H40C 109.5 . .
H40A C40A H40C 109.5 . .
H40B C40A H40C 109.5 . .
C39 C41A H41A 109.5 . .
C39 C41A H41B 109.5 . .
H41A C41A H41B 109.5 . .
C39 C41A H41C 109.5 . .
H41A C41A H41C 109.5 . .
H41B C41A H41C 109.5 . .
C39 C42A H42A 109.5 . .
C39 C42A H42B 109.5 . .
H42A C42A H42B 109.5 . .
C39 C42A H42C 109.5 . .
H42A C42A H42C 109.5 . .
H42B C42A H42C 109.5 . .
C39 C40B H40D 109.5 . .
C39 C40B H40E 109.5 . .
H40D C40B H40E 109.5 . .
C39 C40B H40F 109.5 . .
H40D C40B H40F 109.5 . .
H40E C40B H40F 109.5 . .
C39 C41B H41D 109.5 . .
C39 C41B H41E 109.5 . .
H41D C41B H41E 109.5 . .
C39 C41B H41F 109.5 . .
H41D C41B H41F 109.5 . .
H41E C41B H41F 109.5 . .
C39 C42B H42D 109.5 . .
C39 C42B H42E 109.5 . .
H42D C42B H42E 109.5 . .
C39 C42B H42F 109.5 . .
H42D C42B H42F 109.5 . .
H42E C42B H42F 109.5 . .
C39 C40C H40G 109.5 . .
C39 C40C H40H 109.5 . .
H40G C40C H40H 109.5 . .
C39 C40C H40I 109.5 . .
H40G C40C H40I 109.5 . .
H40H C40C H40I 109.5 . .
C39 C41C H41G 109.5 . .
C39 C41C H41H 109.5 . .
H41G C41C H41H 109.5 . .
C39 C41C H41I 109.5 . .
H41G C41C H41I 109.5 . .
H41H C41C H41I 109.5 . .
C39 C42C H42G 109.5 . .
C39 C42C H42H 109.5 . .
H42G C42C H42H 109.5 . .
C39 C42C H42I 109.5 . .
H42G C42C H42I 109.5 . .
H42H C42C H42I 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.248(3) .
O2 C10 1.374(4) .
O2 C14 1.392(4) .
N1 C4 1.339(3) .
N1 C7 1.404(3) .
N1 H1 0.8800 .
C1 C2 1.462(3) .
C1 C2 1.463(3) 3_666
C1 C1 2.039(5) 3_666
C2 C3 1.390(3) .
C2 C1 1.463(3) 3_666
C3 C4 1.392(4) .
C3 H3 0.9500 .
C4 C5 1.539(3) .
C5 C6 1.515(4) .
C5 C12 1.537(4) .
C5 C13 1.544(4) .
C6 C11 1.381(4) .
C6 C7 1.390(4) .
C7 C8 1.385(4) .
C8 C9 1.390(4) .
C8 H8 0.9500 .
C9 C10 1.381(4) .
C9 H9 0.9500 .
C10 C11 1.399(4) .
C11 H11 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
O3 C16 1.226(4) .
O4 C23 1.238(3) .
N2 C16 1.331(4) .
N2 C15 1.463(4) .
N2 H2N 0.8800 .
N3 C23 1.337(3) .
N3 C24 1.471(3) .
N3 H3N 0.8800 .
C15 C32 1.513(4) 3_666
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.495(4) .
C17 C18 1.388(4) .
C17 C22 1.391(4) .
C18 C19 1.387(4) .
C18 H18 0.9500 .
C19 C20 1.390(4) .
C19 C23 1.493(4) .
C20 C21 1.395(5) .
C20 H20 0.9500 .
C21 C22 1.390(5) .
C21 C39 1.538(4) .
C22 H22 0.9500 .
C24 C25 1.510(4) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C38 1.390(4) .
C25 C26 1.402(5) .
C26 C27 1.432(5) .
C26 C31 1.438(5) .
C27 C28 1.339(7) .
C27 H27 0.9500 .
C28 C29 1.377(8) .
C28 H28 0.9500 .
C29 C30 1.394(8) .
C29 H29 0.9500 .
C30 C31 1.414(5) .
C30 H30 0.9500 .
C31 C32 1.407(5) .
C32 C33 1.398(5) .
C32 C15 1.513(4) 3_666
C33 C34 1.427(5) .
C33 C38 1.448(4) .
C34 C35 1.352(6) .
C34 H34 0.9500 .
C35 C36 1.384(6) .
C35 H35 0.9500 .
C36 C37 1.370(5) .
C36 H36 0.9500 .
C37 C38 1.437(4) .
C37 H37 0.9500 .
C39 C40B 1.402(13) .
C39 C41C 1.41(3) .
C39 C42A 1.417(10) .
C39 C41A 1.437(11) .
C39 C42C 1.480(17) .
C39 C41B 1.532(11) .
C39 C42B 1.694(12) .
C39 C40A 1.695(8) .
C39 C40C 1.76(2) .
C40A H40A 0.9800 .
C40A H40B 0.9800 .
C40A H40C 0.9800 .
C41A H41A 0.9800 .
C41A H41B 0.9800 .
C41A H41C 0.9800 .
C42A H42A 0.9800 .
C42A H42B 0.9800 .
C42A H42C 0.9800 .
C40B H40D 0.9800 .
C40B H40E 0.9800 .
C40B H40F 0.9800 .
C41B H41D 0.9800 .
C41B H41E 0.9800 .
C41B H41F 0.9800 .
C42B H42D 0.9800 .
C42B H42E 0.9800 .
C42B H42F 0.9800 .
C40C H40G 0.9800 .
C40C H40H 0.9800 .
C40C H40I 0.9800 .
C41C H41G 0.9800 .
C41C H41H 0.9800 .
C41C H41I 0.9800 .
C42C H42G 0.9800 .
C42C H42H 0.9800 .
C42C H42I 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88 1.99 2.817(3) 156.2 3_666
N2 H2N O1 0.88 2.63 3.511(3) 176.4 .
N3 H3N O1 0.88 2.13 2.985(3) 165.1 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -0.7(5) . .
C2 C1 C2 C3 -179.3(3) 3_666 .
C1 C1 C2 C3 -179.3(3) 3_666 .
O1 C1 C2 C1 178.6(4) . 3_666
C2 C1 C2 C1 -0.002(0) 3_666 3_666
C1 C2 C3 C4 173.6(2) . .
C1 C2 C3 C4 -5.4(5) 3_666 .
C7 N1 C4 C3 -174.2(2) . .
C7 N1 C4 C5 5.3(3) . .
C2 C3 C4 N1 2.1(4) . .
C2 C3 C4 C5 -177.3(2) . .
N1 C4 C5 C6 -7.2(3) . .
C3 C4 C5 C6 172.3(2) . .
N1 C4 C5 C12 -130.4(2) . .
C3 C4 C5 C12 49.1(3) . .
N1 C4 C5 C13 108.5(2) . .
C3 C4 C5 C13 -72.0(3) . .
C12 C5 C6 C11 -52.2(4) . .
C4 C5 C6 C11 -175.0(3) . .
C13 C5 C6 C11 69.4(4) . .
C12 C5 C6 C7 129.5(2) . .
C4 C5 C6 C7 6.7(3) . .
C13 C5 C6 C7 -108.9(3) . .
C11 C6 C7 C8 -0.3(4) . .
C5 C6 C7 C8 178.2(3) . .
C11 C6 C7 N1 177.3(2) . .
C5 C6 C7 N1 -4.2(3) . .
C4 N1 C7 C8 176.6(3) . .
C4 N1 C7 C6 -0.8(3) . .
C6 C7 C8 C9 0.2(5) . .
N1 C7 C8 C9 -176.9(3) . .
C7 C8 C9 C10 -0.2(5) . .
C14 O2 C10 C9 -160.7(3) . .
C14 O2 C10 C11 18.7(5) . .
C8 C9 C10 O2 179.8(3) . .
C8 C9 C10 C11 0.4(5) . .
C7 C6 C11 C10 0.4(4) . .
C5 C6 C11 C10 -177.7(3) . .
O2 C10 C11 C6 -179.9(3) . .
C9 C10 C11 C6 -0.5(5) . .
C16 N2 C15 C32 -143.7(3) . 3_666
C15 N2 C16 O3 8.8(5) . .
C15 N2 C16 C17 -171.2(3) . .
O3 C16 C17 C18 160.0(3) . .
N2 C16 C17 C18 -20.0(4) . .
O3 C16 C17 C22 -21.4(4) . .
N2 C16 C17 C22 158.6(3) . .
C22 C17 C18 C19 1.8(4) . .
C16 C17 C18 C19 -179.6(2) . .
C17 C18 C19 C20 -1.5(4) . .
C17 C18 C19 C23 177.8(2) . .
C18 C19 C20 C21 -0.9(4) . .
C23 C19 C20 C21 179.7(3) . .
C19 C20 C21 C22 3.0(5) . .
C19 C20 C21 C39 -176.7(3) . .
C20 C21 C22 C17 -2.7(5) . .
C39 C21 C22 C17 176.9(3) . .
C18 C17 C22 C21 0.4(5) . .
C16 C17 C22 C21 -178.3(3) . .
C24 N3 C23 O4 -0.4(5) . .
C24 N3 C23 C19 178.6(3) . .
C18 C19 C23 O4 -157.7(3) . .
C20 C19 C23 O4 21.7(4) . .
C18 C19 C23 N3 23.4(4) . .
C20 C19 C23 N3 -157.2(3) . .
C23 N3 C24 C25 143.2(3) . .
N3 C24 C25 C38 110.6(3) . .
N3 C24 C25 C26 -72.0(4) . .
C38 C25 C26 C27 176.0(2) . .
C24 C25 C26 C27 -1.4(4) . .
C38 C25 C26 C31 -2.0(4) . .
C24 C25 C26 C31 -179.4(2) . .
C25 C26 C27 C28 -178.8(3) . .
C31 C26 C27 C28 -0.7(4) . .
C26 C27 C28 C29 -3.1(5) . .
C27 C28 C29 C30 3.0(6) . .
C28 C29 C30 C31 1.0(6) . .
C29 C30 C31 C32 173.0(3) . .
C29 C30 C31 C26 -4.6(5) . .
C25 C26 C31 C32 4.8(4) . .
C27 C26 C31 C32 -173.2(2) . .
C25 C26 C31 C30 -177.5(3) . .
C27 C26 C31 C30 4.4(4) . .
C30 C31 C32 C33 179.3(3) . .
C26 C31 C32 C33 -3.1(4) . .
C30 C31 C32 C15 -4.4(4) . 3_666
C26 C31 C32 C15 173.1(2) . 3_666
C31 C32 C33 C34 177.0(2) . .
C15 C32 C33 C34 0.7(4) 3_666 .
C31 C32 C33 C38 -1.3(4) . .
C15 C32 C33 C38 -177.6(2) 3_666 .
C32 C33 C34 C35 -178.7(3) . .
C38 C33 C34 C35 -0.4(4) . .
C33 C34 C35 C36 -2.8(5) . .
C34 C35 C36 C37 2.7(5) . .
C35 C36 C37 C38 0.6(5) . .
C26 C25 C38 C37 179.9(2) . .
C24 C25 C38 C37 -2.7(4) . .
C26 C25 C38 C33 -2.4(4) . .
C24 C25 C38 C33 174.9(2) . .
C36 C37 C38 C25 174.0(3) . .
C36 C37 C38 C33 -3.7(4) . .
C32 C33 C38 C25 4.1(4) . .
C34 C33 C38 C25 -174.2(2) . .
C32 C33 C38 C37 -178.1(2) . .
C34 C33 C38 C37 3.5(4) . .
C22 C21 C39 C40B 6.6(8) . .
C20 C21 C39 C40B -173.7(7) . .
C22 C21 C39 C41C -96.4(13) . .
C20 C21 C39 C41C 83.3(13) . .
C22 C21 C39 C42A 95.1(7) . .
C20 C21 C39 C42A -85.2(7) . .
C22 C21 C39 C41A -138.5(6) . .
C20 C21 C39 C41A 41.2(7) . .
C22 C21 C39 C42C 71.7(9) . .
C20 C21 C39 C42C -108.7(9) . .
C22 C21 C39 C41B -122.5(7) . .
C20 C21 C39 C41B 57.2(7) . .
C22 C21 C39 C42B 127.5(6) . .
C20 C21 C39 C42B -52.8(6) . .
C22 C21 C39 C40A -20.5(5) . .
C20 C21 C39 C40A 159.2(4) . .
C22 C21 C39 C40C 169.0(7) . .
C20 C21 C39 C40C -11.4(8) . .
